Honors College Thesis
 

Chemical screening of the secondary metabolites of Streptomyces cellulosae

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  • The purpose of this project was to isolate gabosines and other compounds through chemical screening of secondary metabolites of Streptomyces cellulosae subsp. griseorubiginoses strain S1096. Two different media were used to cultivate S. cellulosae. The first contained soybean and mannitol. The other contained oatmeal and trace element solution. After cultivation the contents of each were centrifuged and lyophilized. Column chromatography was employed to fraction out the oatmeal based metabolites (OBM) and the soybean based metabolites (SBM). The OBM TLC indicated several potential compounds in the eluted fractions. 1H NMR analysis showed the first to be gabosine B. The second could not be found to match prior gabosines or other compounds in 1H NMR analysis. Further analysis using HSQC, HMBC, NOESY, and 1D nOe techniques revealed the structure of the molecule and its stereochemistry. The compound has the same structure as streptol and 1-epi-valienol, but the stereochemistry is different, establishing it as a new member of the gabosine family of natural products. For the secondary metabolites extracted from the SBM, TLC showed one large promising group of fractions. 1H NMR analysis indicated a mixture of three compounds, one of which was Gabosine B. High Performance Liquid Chromatography (HPLC) was attempted to separate the two unknown compounds, but after separation the purified compounds had low yields and only one could be identified as gabosine A.
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